Polycyclic musks are synthetic fragrances, used in many consumer products, that have been frequently detected in surface waters due to lack of removal during wastewater treatment. The goals of the present study are to characterize the photoproducts (PP) formed during ultraviolet (UV) photolysis, a common disinfection method used by wastewater treatment plants, and to assess the biological effects of the parent compounds and their PP. Photolysis of 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (AHTN, tonalide) and 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[γ]-2-benzopyran (HHCB, galaxolide), the two most common polycyclic musks, was studied using UV-254 irradiation. Parent compound degradation and PP formation were monitored using high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). Tonalide (t<sub>1/2</sub> = 0.58 s, m/z 258) has three major PP (m/z 256, 272, and 272.) Galaxolide (t<sub>1/2</sub> = 8.4 min, m/z 258) has four major PP (m/z 274, 288, 288, and 290). Ion fragmentation patterns were used to propose structures for each PP. Biological activity of both parent compounds and photoproduct mixtures was assessed using human estrogen and retinoid X receptor beta reporter assay systems (Indigo Biosciences).

Photolysis and biological activity of the polycyclic musks tonalide and galaxolide

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.